Hilariously Bad Celebrity Photo Fails That Should Have Never Happened

In a life that’s loaded with professional photoshoots, top-level photo retouchers, and highly-paid paparazzi, there’s just no excuse for a bad snap when you’re a celebrity. Somehow, these painfully awkward pictures saw the light of day and were forever cemented into Internet history. How was this allowed to happen? Whether they’re due to poor retouching or simply bad choices, these awkward celebrity photo fails are hilarious.

Ariana Should See A Doctor For Those Hands

Celebrities may bask in the glow of the camera flash, but not every picture is a winner. In this epic Photoshop fail, Ariana Grande’s hands look massive. We’re not really sure what’s going on, but she definitely pulls off the Hamburger Helper look.

Interestingly, Kim Kardashian was accused of ripping off this photoshoot’s style for her 2018 Kimoji Hearts fragrance promotion. Who rocked the huge hands best?

Taylor Swift Had Cringe-y Prom Photos Like The Rest Of Us

Oh, prom. It’s the highlight of our teen lives. Between the tacky, bedazzled dresses and ill-advised spray tans, most of us cringe when we look back on that defining high school moment. Pop Queen and zillion-time Grammy winner Taylor Swift is no different. Before crafting a signature style and cropping her long locks into a chic lob, she was an average teen (as average as a teen can get when she’s got a country radio hit).

Her prom photos check all the embarrassing teen boxes – the fake gang signs, the satin dress, her date’s sideways baseball cap, the fact that they’re wearing all white, and the citronella tiki torch. It’s all pretty bad.

We Are All Bill Murray And This Baby

This baby must have truly believed he was stuck in Groundhog Day because the second he saw Bill Murray, he was all tears. Most of us would be utterly thrilled to meet the Ghostbusters legend – but not this kid. According to Laura B, who originally submitted the photo to the Tumblr account “Reasons My Son Is Crying,” the toddler’s tears were due to meeting the real-life legend in the flesh. Maybe he remembers Murray’s Christmas Netflix special.

Murray decided to sooth the bawling tot by throwing a parenting Hail Mary: he sobbed in an effort to confuse the kid. As it turns out, it didn’t work, but it did make for a really awkward photo.

Kelly Kapowski Should’ve Left This Picture In The ’90s

Kelly Kapowski was the bombshell of Bayside High. Unfortunately, she followed in the footsteps of her fellow peers who peaked in high school with an awkward nude photoshoot. This 90s-tastic photo features Saved By The Bell actress Tiffani Thiessen squatting in the bushes and covering her body with a large sunhat.

Some questions: what were the moments preceding this shot like? Is this a headshot for a Naked and Afraid casting call? What does the dandelion in her mouth taste like? Are there ants? There are always ants. Tiffani, you deserve better.

Sarah Jessica Parker Needs A Bathroom, Stat!

This photo isn’t inherently awkward if you picture Sarah Jessica Parker in 2018. In the days of Instagram, there’s nothing quite like a Runyon Canyon workout shot to help celebs hawk their Flat Tummy Tea (link in bio!). Unfortunately, in the ’80s and ’90s, this was crazy awkward.

Without Instagram, this was a conscious choice from a professional photographer (i.e. someone asked her to look this sweaty and squat like she was about to pee herself and collapse at the same time). Between the blotches of perspiration on her torso and the fact that bathrooms are scarce up there, it’s just so bad.

Hey Girl, Can You See Me Now?

Hey girl, I dreamt we were waking up together in a quaint bed and breakfast off the coast of Nantucket, when you opened the window to let the smell of the sea breeze into our sunlit room. You smiled coyly in your pajamas before we fell into a deep discussion about how society fosters toxic masculinity.

Then, I wrapped myself in the duvet that matched the wall. Girl, can you even see me? I feel like you can see me even when my heart is totally camouflaged by tacky floral prints. Sorry, Ryan Gosling, you’re a total dreamboat but this is so, so bad.

Despite All My Rage I Am Still Just Nicolas Cage

Nicolas Cage is deeply misunderstood. Sure, the dude spends a fair portion of his life plotting to steal the Declaration of Independence, but he’s really just a sensitive homebody. The real Nicolas Cage can’t be caged into a narrow definition of action hero. He deserves to be afforded the same opportunity to pose with his cat in a red sweater that everyone else does.

We’re not exactly sure where this painfully awkward photo came from, but the cat is clearly stealing the show just as furiously as Cage steals priceless pieces of American history. This photo is a national treasure in itself.

Free As A Bird

Talk about the most unlikely pairing in the world – Mike Tyson, the dude known for biting off someone’s ear in the boxing ring, and a couple of pigeons. As it turns out, Tyson adores pigeons. This much we learned from his Animal Planet series Taking on Tyson. He’s been raising the birds since he was a child and is deeply embroiled in the world of competitive pigeon racing.

The real awkwardness of this precious collection of photos is the fact that it exists at all – Mike Tyson, a prized pigeon racer, forcing his pigeons to kiss? It does not compute. It’s like we just found out the Pigeon Man from Hey Arnold is real and it turns out to be a champion boxer.

What Is Going On In This Photo Of Melissa Joan Hart?

Sabrina The Teenage Witch was a staple in the ’90s, but even the strongest spell couldn’t stop this awful, tacky photoshoot from waving its ’90s freak flag. What is going on and why was this allowed to happen?

This picture of Sabrina actress Melissa Joan Hart pretty much defines the era – a time where teen celebrities didn’t have to choose between straight and crimped hair because they got to have both. Her body language is even more perplexing than her mane. She’s crawling on the ground like cat, yet Salem is nowhere in sight. The trees look rather mystical, but where is this actually supposed to be? Don’t pretend for a second that Sabrina didn’t live in the boring old suburbs. Maybe this is what happened once she jumped into her closet portal?

Michael Jackson Phone Home

In a way, this photo makes sense. The year we were gifted with Michael Jackson’s seminal album Thriller (and the epic zombie dance that became a Halloween party staple), we were also introduced to E.T. The Extra-Terrestrial. The 1982 Stephen Spielberg masterpiece changed the way we look at alien flicks.

The weirdness in this snap is actually pretty heart-warming. It’s like two kindred spirits finally found each other. Jackson never fully felt understood, just like our favorite friendly alien. We’re not even totally sure Jackson was of this planet. He did coin the moon walk move, after all. That has to count for something.

Cleanup In Aisle DiCaprio

Grocery shopping with Leonardo DiCaprio isn’t really something we ever pictured until now. This bizarre photoshoot is somehow nothing and everything we wanted all at once. There’s something we can’t put our finger on about this Tiger Beat prince splaying himself across a very disorganized produce display at our local Kroger.

Part of us wants to scream “cleanup in aisle sexy,” and part of us wants to shyly pluck a fresh banana from his hand and walk away with a healthy, low-calorie bite. Either way, Leonardo DiCaprio is looking like a total snack in this bizarre photoshoot. We certainly could use more fruit in our diets after this one.

Three Kardashians, Five Legs

Photo credit: Calvin Klein / Promotional image

This Calvin Klein photoshoot was a big deal in Kardashian world. Around this time, Kylie Jenner was secretly hiding her pregnancy (that all of us knew about anyway). For most of us, this photoshoot completely confirmed it. The younger Kardashian was one of the only sisters to sneakily conceal her tummy while the rest of the gang posed in their undies and showed off their killer abs.

While Kylie was gaining a member of her family, she was losing something else. Apparently, the person who Photoshopped this look made a major oops and accidentally chopped off her leg. You can’t win ’em all.

He Used To Call You On Your Shellphone

Apparently, Leonardo DiCaprio isn’t a stranger to embarrassing, corny photoshoots. At this point, we wouldn’t be shocked to find out all of his professional pictures from the ’90s were taken in local grocery stores or dollar stores. In this bizarre professional photograph, DiCaprio coyly calls his mermaid queen on a shell phone. Maybe he found it at the bottom of the ocean in Titanic.

If Leo looks sad it’s probably because he is. No one told him shell phones don’t actually work two ways. You can hear the ocean, but under no circumstances can it hear you. Sorry, buddy. In any event, we can forgive this snapshot solely on his soaking-wet hair. Delicious.

Someone Teach Mom How To Photoshop

It’s no secret that the Kardashians spent a lot of money on their looks, between the daily hair and makeup and personal training workouts. It’s just a shame Kris Jenner didn’t splurge for a Photoshop expert because she took her family’s penchant for Facetune a little too far with this Instagram snap.

As soon as Jenner posted the picture, fans noticed her arm looked a little wonky. Sure, it was skinny. It was also bumpy in a way that tells us she tried to shrink it in the app and probably wasn’t wearing her glasses when she checked to make sure it looked natural.

If Life Gives You Limes

Photo credit: Sauza 901 / Promotional image

Justin Timberlake has done a lot of ridiculous things: that [expletive] in a box Saturday Night Live skit, his Super Bowl Selfie, and the era of ramen noodle hair. This bizarre lime picture was taken approximately 15 A.R.N (after Ramen Noodles) as part of a Cinco De Mayo-themed mockumentary promoting Timberlake’s tequila brand. Yes, Timberlake has his own Tequila called Sauza 901.

In the mockumentary, Timberlake stars as Rick “Sour” Vane, a lime with an inexplicable New York accent. It’s slightly uncomfortable, but also definitely worth the watch. Timberlake may even look better dressed as a lime than as noodle soup. What food will he try on next?

How Far Is Heaven From The Bronx?

Jennifer Lopez, the Bronx-born girl-next-door, looks like she fell straight out of heaven in this awkward AF photoshoot. Here’s where things went wrong: the thin, curly hair (when we know Jenny has luxurious, thick locks), the oil (which we can only assume is some sort of after-birth from the heavenly Gods above) and the lone nipple peeking out from behind her perfect arm (which has since been covered out of respect for our queen).

As cringe-worthy as the photo is, it’s impossible to date considering J-Lo hasn’t aged a stitch in the last 25 years. Somehow, other snaps from this photoshoot didn’t come out nearly as awkward – especially when she wipes off the oil and plays some lute.

Celine Dion’s Crafty Ensemble

Our hearts may go on, but we’ll never get over this bizarre photo of Celine Dion. Celine Dion is the epitome of class. The 50-year-old singer is so poised and so renowned that she’s had a residency at Caesars Palace in Las Vegas for the last seven years. That’s some career, which has been done zero justice by this photo.

Celine Dion is not a lady of D.I.Y., yet the frilly layered blouse and rope headband scream “I don’t have a wardrobe budget yet.” Luckily, Celine’s fashion choices got exponentially better over the years.

Someone Send Help For Christina Aguilera

Christina Aguilera was once a fresh-faced teen navigating the utterly bizarre world of early ’00s photoshoots. In this particular image, her legs have inexplicably been amputated by a glass bubble. Don’t worry though. What she’s missing from the bottom, she’s gained on top. Her signature platinum blonde locks are covered by a tall, feather hat.

The most baffling part of this picture is X-Tina’s gloves: they cover just her fingers, not the thumbs. It’s almost as if she’s trying to get away with a crime where she won’t be aided by her opposable thumbs (perhaps typing out a sinister AOL Instant Message with one finger?). Either way, Christina appears to be caught white-handed. Her hands are up and she’s admitted defeat. Better luck next time.

We’re Worried For Beyonce’s iPhone

Beyoncé is a queen who can do no wrong. Unless it comes to Photoshop. Girl, this is why we hire teams to handle our social media. The Lemonade singer caught a whole lot of flak after posting this summery Instagram photo which appears to be completely altered.

It’s not totally clear what Bey tried to do in this photo, but fans are guessing she tried to shrink the size of her calves. While her crooked wine glass could simply be some sort of asymmetrical crystal used by hip-hop royalty, the bending iPhone is a dead giveaway. Just look at the seam on the couch!

Remember That Time Hulk Hogan Sold Pasta?

There was once a time when Hulk Hogan took a break from the WWE and ventured into the world of restauranteurs. He opened Hulk Hogan’s Pastamania in the Mall of America food court. The restaurant offered a bizarre spattering of international pastas including Swedish Meatballs and Pasta Mexican. Whatever Pasta Mexicana is sounds truly horrific.

The “Main Event” (that’s “main course” for the rest of us who aren’t running a schmaltzy pasta shop) included Hulk’s Power Pasta (penne, chicken and veggies) with a menu for “Little Pastamaniacs” (i.e. children) featuring Hulkaroni & Cheese. Honestly, the whole thing was weird. It completely failed, and all we got was this bizarre photo and some indigestion.